NEOANDROGRAPHOLIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H40O8
Molecular Weight	480.591
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CCC(=C)[C@@H](CCC3=CCOC3=O)[C@]1(C)CCC[C@@]2(C)CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

InChI

InChIKey=YGCYRQKJYWQXHG-RDNQFMDVSA-N

InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19-,20-,21+,22-,24-,25+,26+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17109078
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17436371 | https://www.ncbi.nlm.nih.gov/pubmed/20446243 | https://www.ncbi.nlm.nih.gov/pubmed/17165582

Neoandrographolide, one of the principal diterpene lactones, isolated from a medicinal herb Andrographis paniculata Nees. Andrographis paniculata (Burm. f.) Wall. ex Nees (Acanthaceae), also known as “kalmegh” in India, is a widely distributed plant in Asia. In many traditional formulations, the aerial parts have been used as anti-inflammatory and antipyretic drugs for the treatment of a variety of chronic and infectious diseases. Neoandrographolide possesses significant anti-inflammatory effects, which implies that it would be one of the major contributing components to participate in the anti-inflammatory effect of A. paniculata. and a potential candidate for further clinical trial.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
lipopolysaccharide-mediated signaling pathway 1 Target ID: GO:0031663 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17109078	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Different AhR binding sites of diterpenoid ligands from Andrographis paniculata caused differential CYP1A1 induction in primary culture in mouse hepatocytes.	2011 Dec	21963808

Patents

Sample Use Guides

In Vivo Use Guide

Ear Edema was induced in BALB/c mice by topical application of dimethyl benzene (50 mkl). Neoandrographolide was administered orally (50, 100 and 150 mg/kg) 1 hour before the application of dimethyl benzene.

Route of Administration: Oral

In Vitro Use Guide

Stimulation of RAW 264.7 macrophages with phorbol-12-myristate-13-acetate (PMA) resulted in detectable respiratory bursts measured by a luminol-enchanced method. neoandrographolide from 7.5 to 150 mkM, showed a dose dependent suppression of the respiratory burst effect on macrophages

Name

Type

Language

NEOANDROGRAPHOLIDE

Common Name

English

2(5H)-FURANONE, 3-(2-(5-((.BETA.-D-GLUCOPYRANOSYLOXY)METHYL)DECAHYDRO-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYL)-, (1R-(1.ALPHA.,4A.BETA.,5.ALPHA.,8A.ALPHA.))-

Systematic Name

English

NEOANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC]

Common Name

English

5.BETA.,9.BETA.H,10.ALPHA.-LABDA-8(20),13-DIEN-16-OIC ACID, 18-(GLUCOSYLOXY)-15-HYDROXY-, .GAMMA.-LACTONE

Systematic Name

English

2(5H)-FURANONE, 3-(2-((1R,4AS,5R,8AS)-5-((.BETA.-D-GLUCOPYRANOSYLOXY)METHYL)DECAHYDRO-5,8A-DIMETHYL-2-METHYLENE-1-NAPHTHALENYL)ETHYL)-

Systematic Name

English

NEOANDROGRAPHISIDE

Common Name

English

(-)-NEOANDROGRAPHOLIDE

Common Name

English

Code System Code Type Description

CAS

27215-14-1